What to Wear with Chelsea Boots Men

INTRODUCTION: Chelsea boots look formal and classic; however, you can wear them with both formal and casual trends. Chelsea boots are perfect for every man, it does not matter if you wear jeans or suits, and these boots will always look good on you.

With their simple and clean style, Chelsea boots can be worn as career or dress boots, for those who hate boots with laces, I suggest you opt for Chelsea boots because they have no laces.

You can wear these boots with skinny jeans, straight leg relaxed jeans, suits and chino pants. So if you want to dress to impress, you can opt for any on these top ten Chelsea boots I have listed here.


Today on Olixe, I have compiled a list of the best Chelsea boots every man would love to wear, your choice for boots might be different from mine, but I’m 100% sure that you will not fail to find your test on this list.


What to Wear with Chelsea Boots Men

What to Wear with Chelsea Boots Men


NOTE: Links to stores where you can buy these Chelsea Boots for men are listed at the end of this post.



  1. 1. Chelsea Boot

Chelsea Boot 1




Simplicity and class is what I consider when grading shoes, this Chelsea boot from Prada makes it to the top ten list of the best Chelsea boots. It comes in black only, however black is a neutral color, so it will match with everything. The boot features glowing leather upper and a rubber sole which makes them durable and classy, the shining leather will look good on formal outfits. If you’re looking for work shoes, dress boots or career shoes, please, consider this boot because it has a versatile design.

What to wear with this black Chelsea boot?

Tip 1: Team these black Chelsea’s with a grey slim fit suit. Then complement the grey suit with a pink dress shirt and accessorize with a slim black tie.

Tip 2: You can wear them with flat front trousers. In this case complement your trousers with a cufflink dress shirt and a tweed jacket.

Tip 3: If you love wearing chinos to work, then these black Chelsea boots will match with fitting chino pants. To look fashionable, you can match your brown chinos with a sky-blue dress shirt, then wear a navy blue double breast coat and a red check slim tie.

  1. 2. Chelsea Boot

Chelsea Boot 5

This is my favorite color when it comes to boots and dress shoes. It has this brogue style on the front which makes it unique and easy to match with both formal and casual outfits. The boot features a shinning brown leather upper, leather sole and leather lining. You can wear this brown boot with jeans, suits and classy chino pants.

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Styling tips for this brown Chelsea Boot:

Tip 1: If you’re great fan of jeans, this boot will match well with formal straight leg jeans. To look smart and formal, you can wear a white or pink dress shirt and complement the boots with a brown leather belt.

Tip 2: You can also wear them with a suit, in this case, we should opt for a grey or navy blue suit, also a black suit will match but not as good as Grey & Navy Blue.

Tip 3: How about teaming it with a dark pink trouser, I know the color sounds strange, but if you complement it well, you will look fabulous. For example, you wear a white slim-fit dress shirt with your pink trousers; and then wear a dark yellow sleeveless sweater over the white shirt and a green double breast jacket over the sweater. This is a color blocking trend, so if you’re not comfortable with bright colors, please opt for dark ones.

  1. 3.

    Ring’ Boot

Chelsea Boot 2

This sleek leather Chelsea boot has a versatile design, you can wear it to any occasion. For those who want to wear boots with skinny jeans, you should try out these sharp Chelsea boots. It features an elastic gore which ensures that the boots fit you well, soft leather upper, leather and rubber sole for durability and quality.

So, what can you wear with these black sharp Chelsea boots:

Tip 1: In my opinion, I would team them with grey skinny jeans, and then complement my jeans with a white slim fit t-shirt and a black leather jacket or blazer.

Tip 2: If I wanted to wear them to work or business meeting, I would pull them with a black slim fit suit and a maroon / blue dress shirt, then accessorize with a black slim tie.

  1. 4.

    Desperado’ Chelsea Boot

Chelsea Boot 5

This Desperado’ Chelsea Boot is more of a casual Chelsea boot, so you can team it with trendy casual outfits. The boot features soft leather upper and leather sole. The elastic gores make it easy to wear the boots. When it comes to styling, you can wear this brown Chelsea casual boot with denim jeans. To look fashionable, you can complement the trend with denim designer shirt, if its a long sleeved shirt, fold the sleeves of the shirt. Then for the jeans, opt for boot-cut jeans because they drape well on such boots.

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For those who want to wear brown Chelsea boots with suits, I’m not sure if this Desperado’ Chelsea Boot will look good on suits. I suggest you opt for boot in position (2)

  1. 5.

    Neal’ Wingtip Chelsea Boot

Chelsea Boot 4

I’m a great fan of oxford shoes and this Chelsea boot is a combination of oxford style and Chelsea. It’s a cool casual boot which can match with trendy casual outfits. It’s versatile styles makes it a must have boot in every guy’s collection. The boot has a mildly distressed design and the brown leather / rubber sole just adds value to the boot making it unique. When it comes to comfort, no Chelsea boot beats this Neal’ Wingtip Chelsea Boot. The boot features weathered suede upper, leather lining and a rubber sole.

What to wear with this black Neal’ Wingtip Chelsea Boot?

Tip 1: It is a casual boot, so it will look good when matched with trendy jeans. However, this boot has a distressed style, so damages jeans, twisted boot cut jeans and distressed jeans will match with this boot. You can add value to your style by wearing a designer t-shirt with your jeans and complement the boots with a black suede casual belt.

For those who love wearing skinny jeans with Chelsea boots, I suggest you opt boots in position (10)

  1. 6. Sunday – Chelsea Boot

Chelsea Boot 6

Now, this is the type of Chelsea boot you can wear with both suits and jeans. It’s a classy boot which features calf leather upper, leather lining and a stitched leather sole. This Sunday – Chelsea Boot comes in four different colors and these include black leather, brown suede, brown leather and tan leather, so you will have more than one option. So if you’re looking for fashion boots to wear on weekends with those trendy denim jeans or men’s dress boots for work, look no further, this is the right Chelsea boot for you.

Note: If you team these boots with jeans, make sure that you opt for jeans with a formal classy style. Avoid wearing distressed or damaged jeans with such boots opt for the simple fade or no fade straight denim jeans and complement the boots with a matching leather belt.

If i was to wear these boots with jeans to work or on weekends, I could pull them with a dark denim blue jean and a check long sleeved shirt.

  1. 7.

    Bass Men’s Amsterdam Ankle Boot

Chelsea Boot 7

These black Chelsea boots can match with both skinny jeans and suits or trousers. I love the style and shape of these boots, the sharp pointed toe makes them look trendy, and they also have high quality soft leather upper and a rubber sole which makes them durable. Unlike most Chelsea boots, you will not spend more than $100 on this Bass Men’s Amsterdam Ankle Boot, it comes at an affordable price yet it looks cool. So combining its elegance and affordability, this Bass Men’s Amsterdam Ankle Boot makes it to the top ten Chelsea boots for men.

  1. 8.

    STRATFORD – Wing Tip Chelsea Boot

Chelsea Boot 8

Wing tip Chelsea boots tend to stand out from the rest of Chelsea boots. Men, if you want to dress to impress women and people around you, then opt for this Wing tip boot. Judging from its style, you can team it with both jeans and formal outfits like flat front trousers or suits. Since these boots are brown, you will look fashionable if you team them with a navy blue slim-fit suit, grey suit, denim blue straight leg denim jeans, black jeans or trousers. However, you should always remember to complement them with a brown leather smart belt.

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This STRATFORD Wing Tip Chelsea Boot features a durable rubber sole, leather upper, leather lining and a brogue style. You can wear them both on weekends and work days.

  1. 9.

    Hudson ‘Moran’ Chelsea Boots

Chelsea Boot 9

They might not look that classy, but i lets be fair to those guys who wear skinny jeans, most of the chelsea boots listed on here cater for suits and straight leg jeans, but this Hudson ‘Moran’ Chelsea Boot will match with your skinny jeans. They feature a soft leather upper, pointed sharp toe, and a rubber sole, make sure you opt for a larger size than your normal shoes because this pointed toe makes the boots tight.

  1. 10.

    Juan’ Low Chelsea Boots

Chelsea Boot 10

A bit different from boots in position (9) , these short Chelsea suede upper boots will match with both jeans and chino pants. They have a trendy casual style, so you can wear them with jeans to work. So if you’re not comfortable with ankle boots, they opt for these short boots which stop just below the ankle. A navy blue velvet blazer will look good with these Juan’ Low Chelsea Boots.


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